Diethyl Ether → HCID 67925099, compound

HRID 344690Notes

Reaction equation

HRID 344690 reaction equation
C[N:2]1[CH2:7][CH2:6][CH:5]=[C:4]([C:8]2[S:9][CH:10]=[C:11]([CH3:13])[N:12]=2)[CH2:3]1.[Cl:14]C(OC(Cl)C)=O.CCOCC>ClC(Cl)C>[ClH:14].[CH3:13][C:11]1[N:12]=[C:8]([C:4]2[CH2:3][NH:2][CH2:7][CH2:6][CH:5]=2)[S:9][CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5213051-Chloroethyl chloroformateHCID 54366899HCID 54366899, compound

Product 1

HCID 67925099HCID 67925099, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

3.64 g of [1-methyl-3-(4-methylthiazol-2-yl)-1,2,5,6-tetrahydropyridine] is dissolved in 70 cm3 of dichloroethane, 2.95 g of alphachloroethyl chloroformate is added at 0° C. under inert atmosphere, and the whole is heated under reflux for one hour 30 minutes. The solvent is eliminated, te residue is taken up with ether and filtered. The filtrate is concentrated to dryness, the residue is taken up in 40 cm3 of methanol and heated for 30 minutes under reflux. The solvent is eliminated and the residue is crystallized twice from ethanol and ether and 2.67 g of expected product is obtained. M.p.=184°-185° C. (decomp.).

Workup

  1. temperaturethe whole is heated
  2. temperatureunder reflux for one hour 30 minutes
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated to dryness
  5. temperatureheated for 30 minutes
  6. temperatureunder reflux
  7. customthe residue is crystallized twice from ethanol and ether

Sources & evidence

ORD record
ord-7808c326d15147d7b34d3cfe83e3dfcf
Source dataset
uspto-grants-1991_10
Patent number
US05053416

Reaction notes

Loading…